ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-glucopyranoside | 3945-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-amino-6-ethylsulfanyloxan-2-yl]methyl acetate
• CAS: 3945-29-7
• 化学式: C₁₄H₂₃NO₇S
• 分子量: 349.405
• InChiKey: PURAQAKRKIRZII-KSTCHIGDSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  448.8±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以95%的产率得到乙基3,4,6-三-O-乙酰基-2-乙酰氨基-2-脱氧-beta-D-硫代吡喃葡萄糖苷
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353
• 作为产物：
  描述：

  在 水 作用下， 以 四氢呋喃 为溶剂， 以11 mg的产率得到ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The Mild Cleavage of 2-Amino-2-deoxy-d-glucoside Methoxycarbonyl Derivatives

  摘要：

  [GRAPHICS]The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl3 and triethylamine in dry THF at 60 degrees C and subsequent aqueous hydrolysis yields the free amine in 54 to 93% yields. The selective cleavage of methyl carbamates with MeSiCl3 in the presence of a 2,2,2-trichloroethoxycarbonyl group or 2-azido glycosides affords selectively, orthogonal N-deprotected carbohydrates.

  DOI：

  10.1021/ol0063353

文献信息

• Syntheses of l-glucosamine donors for 1,2-trans-glycosylation reactions
  作者：Dominique Lafont、Paul Boullanger

  DOI：10.1016/j.tetasy.2006.12.011

  日期：2006.12

  Two new L-glucosarnine donors, that is pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta-L-glucopyranoside 16 and ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-l-thio-beta-L-glucopyranoside 21 were prepared in 12 steps from L-arabinose. The reaction pathway uses 3,4,6-tri-O-acetyl-L-glucal 5, and then 3,4,6-tri-O-acetyl-2-deoxy-2-iodO-alpha-L-mannopyranosyl azide 8 as intermediates. The latter, together with donors 16 and 21, were used for preparing L-glucosamine neoglycolipids. (c) 2007 Elsevier Ltd. All rights reserved.